Production process of N-substituted amide compounds

• US 4,835,312 A
• Filed: 07/02/1986
• Issued: 05/30/1989
• Est. Priority Date: 01/17/1981
• Status: Expired due to Fees

• Current Assignee: Mitsui Chemicals Incorporated (Mitsui Chemicals)
• Original Assignee: Mitsui Chemicals Incorporated (Mitsui Chemicals)
• Inventors: Itoh, Hiroshi, Nitta, Atsuhiko, Nakagawa, Toshimi
• Primary Examiner(s): Hines, Robert V.
• Application Number:
  US06/881,087
• Time in Patent Office: 1,063 Days
• Field of Search: 564/204, 564/205, 564/142, 564/207, 564/143, 564/80
• US Class Current: 564/205
• CPC Class Codes: C07C 255/00 Carboxylic acid nitriles cyanogen or compounds thereof C01C3/00
• CPC Class Codes: C07C 273/1863 from urea
• CPC Class Codes: C07C 275/06 of an acyclic and saturated carbon skeleton
• CPC Class Codes: C07D 209/86 with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
• CPC Class Codes: C07D 219/14 with hydrocarbon radicals, substituted by nitrogen atoms, attached to the ring nitrogen atom

Abstract

An N-substituted amide compound is produced with a high yield by initiating a reaction among a starting amide compound such as a saturated or unsaturated, aliphatic or aromatic carboxylic acid amide, a halogen-substituted compound such as an alkyl halide and a strongly basic substance while maintaining the basic substance in a suspended state.

Claims

1. In a process for producing an unsaturated N-substituted amide compound by bringing a strongly basic substance, a starting amide compound and a halogen-substituted compound into simultaneous contact in an aprotic polar solvent to react them together, the improvement wherein the reaction system the starting amide compound is acrylamide or methacrylamide;

the strongly basic substance is an alkali metal hydroxide;

the halogen-substituted compound is an allyl halide alkyl polyhalide, aralkyl halide or allyl halide compound;

the amount of the strongly basic substance is 0.5-1.5 moles per mole of replaceable hydrogen of the starting amide compound;

the amount of aprotic polar solvent is 10-90% by weight of the whole weight of the reactants including the solvent per se;

the amount of water present at the beginning of the reaction is 5% by weight or less of the reaction system; and

the reaction is initiated while maintaining the basic substance in a suspended state.